Capsaicin (/kæpˈseɪ.ɪsɪn/ (INN);
8-methyl-N-vanillyl-6-nonenamide) is an active component of chili
peppers, which are plants belonging to the genus Capsicum. It is an
irritant for mammals, including humans, and produces a sensation of
burning in any tissue with which it comes into contact.
several related compounds are called capsaicinoids and are produced as
secondary metabolites by chili peppers, probably as deterrents against
certain mammals and fungi. Pure capsaicin is a hydrophobic,
colorless, highly pungent, crystalline to waxy compound.
3.2 Biosynthetic pathway
4 Natural function
5.2 Research and pharmaceutical use
Pepper spray and pests
5.4 Equestrian sports
6 Mechanism of action
7.1 Acute health effects
7.2 Treatment after exposure
7.3 Effects on weight loss and regain
8 See also
10 Further reading
11 External links
The compound was first extracted in impure form in 1816 by Christian
Friedrich Bucholz (1770–1818). He called it "capsicin", after the
Capsicum from which it was extracted. John Clough Thresh
(1850–1932), who had isolated capsaicin in almost pure form,
gave it the name "capsaicin" in 1876. Karl Micko isolated capsaicin
in its pure form in 1898. Capsaicin's chemical composition was
first determined by E. K. Nelson in 1919, who also partially
elucidated capsaicin's chemical structure.
Capsaicin was first
synthesized in 1930 by Ernst Spath and Stephen F. Darling. In
1961, similar substances were isolated from chili peppers by the
Japanese chemists S. Kosuge and Y. Inagaki, who named them
In 1873 German pharmacologist Rudolf Buchheim (1820–1879) and in
1878 the Hungarian doctor Endre Hőgyes stated that "capsicol"
(partially purified capsaicin) caused the burning feeling when in
contact with mucous membranes and increased secretion of gastric acid.
The most commonly occurring capsaicinoids are capsaicin (69%),
dihydrocapsaicin (22%), nordihydrocapsaicin (7%), homocapsaicin (1%),
and homodihydrocapsaicin (1%) 
Besides the five natural capsaicinoids (table below), one synthetic
member of the capsaicinoid family exists: vanillylamide of n-nonanoic
acid (VNA, also PAVA) used as a reference substance for determining
the relative pungency of capsaicinoids.
The general biosynthetic pathway of capsaicin and other capsaicinoids
was elucidated in the 1960s by Bennett and Kirby, and Leete and
Louden. Radiolabeling studies identified phenylalanine and valine as
the precursors to capsaicin. Enzymes of the phenylpropanoid
pathway, phenylalanine ammonia lyase (PAL), cinnamate 4-hydroxylase
(C4H), caffeic acid O-methyltransferase (COMT) and their function in
capsaicinoid biosynthesis were identified later by Fujiwake et
al., and Sukrasno and Yeoman. Suzuki et al. are
responsible for identifying leucine as another precursor to the
branched-chain fatty acid pathway. It was discovered in 1999 that
pungency of chili peppers is related to higher transcription levels of
key enzymes of the phenylpropanoid pathway, phenylalanine ammonia
lyase, cinnamate 4-hydroxylase, caffeic acid O-methyltransferase.
Similar studies showed high transcription levels in the placenta of
chili peppers with high pungency of genes responsible for
branched-chain fatty acid pathway.
Plants exclusively of the
Capsicum genus produce capsaicinoids, which
Capsaicin is believed to be synthesized in the
interlocular septum of chili peppers and depends on the gene AT3,
which resides at the pun1 locus, and which encodes a putative
Biosynthesis of the capsaicinoids occurs in the glands of the pepper
fruit where capsaicin synthase condenses vanillylamine from the
phenylpropanoid pathway with an acyl-CoA moiety produced by the
branched-chain fatty acid pathway.
Capsaicin is the most abundant capsaicinoid found in the Capsicum
genus, but at least ten other capsaicinoid variants exist.
Phenylalanine supplies the precursor to the phenylpropanoid pathway
while leucine or valine provide the precursor for the branched-chain
fatty acid pathway. To produce capsaicin,
8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid
pathway and condensed with vanillamine. Other capsaicinoids are
produced by the condensation of vanillamine with various acyl-CoA
products from the branched-chain fatty acid pathway, which is capable
of producing a variety of acyl-CoA moieties of different chain length
and degrees of unsaturation. All condensation reactions between
the products of the phenylpropanoid and branched-chain fatty acid
pathway are mediated by capsaicin synthase to produce the final
Vanillamine is a product of the phenylpropanoid pathway
Valine enters the branched fatty acid pathway to produce
Capsaicin synthase condenses vanillamine and 8-methy-6-nonenoyl CoA to
Capsaicin is present in large quantities in the placental tissue
(which holds the seeds), the internal membranes and, to a lesser
extent, the other fleshy parts of the fruits of plants in the genus
Capsicum. The seeds themselves do not produce any capsaicin, although
the highest concentration of capsaicin can be found in the white pith
of the inner wall, where the seeds are attached.
The seeds of
Capsicum plants are dispersed predominantly by birds: in
TRPV1 channel does not respond to capsaicin or related
chemicals (avian vs. mammalian
TRPV1 show functional diversity and
selective sensitivity). This is advantageous to the plant, as chili
pepper seeds consumed by birds pass through the digestive tract and
can germinate later, whereas mammals have molar teeth which destroy
such seeds and prevent them from germinating. Thus, natural selection
may have led to increasing capsaicin production because it makes the
plant less likely to be eaten by animals that do not help it
disperse. There is also evidence that capsaicin may have evolved
as an anti-fungal agent: the fungal pathogen Fusarium, which is
known to infect wild chilies and thereby reduce seed viability, is
deterred by capsaicin, which thus limits this form of predispersal
In 2006, it was discovered that the venom of a certain tarantula
species activates the same pathway of pain as is activated by
capsaicin; this was the first demonstrated case of such a shared
pathway in both plant and animal anti-mammal defense.
Because of the burning sensation caused by capsaicin when it comes in
contact with mucous membranes, it is commonly used in food products to
provide added spice or "heat" (piquancy), usually in the form of
spices such as chili powder and paprika. In high concentrations,
capsaicin will also cause a burning effect on other sensitive areas,
such as skin or eyes. The degree of heat found within a food is
often measured on the Scoville scale. Because people enjoy the
heat, there has long been a demand for capsaicin-spiced products
like curry, chili con carne, and hot sauces such as
Tabasco sauce and
It is common for people to experience pleasurable and even euphoric
effects from ingesting capsaicin. Folklore among self-described
"chiliheads" attributes this to pain-stimulated release of endorphins,
a different mechanism from the local receptor overload that makes
capsaicin effective as a topical analgesic.
Research and pharmaceutical use
Capsaicin is used as an analgesic in topical ointments, nasal sprays
(Sinol-M), and dermal patches to relieve pain, typically in
concentrations between 0.025% and 0.1%. It may be applied in cream
form for the temporary relief of minor aches and pains of muscles and
joints associated with arthritis, backache, strains and sprains, often
in compounds with other rubefacients.
It is also used to reduce the symptoms of peripheral neuropathy such
as post-herpetic neuralgia caused by shingles. Capsaicin
transdermal patch (Qutenza) for the management of this particular
therapeutic indication (pain due to post-herpetic neuralgia) was
approved as a therapeutic by the U.S. FDA, but a subsequent
Qutenza to be used as an analgesic in
Although capsaicin creams have been used to treat psoriasis for
reduction of itching, a review of six clinical trials
involving topical capsaicin for treatment of pruritus concluded there
was insufficient evidence of effect.
There is insufficient clinical evidence to determine the role of
ingested capsaicin on a variety of human disorders, including obesity,
diabetes, cancer and cardiovascular diseases.
Pepper spray and pests
Capsaicin is also an active ingredient in riot control and personal
defense pepper spray agents. When the spray comes in
contact with skin, especially eyes or mucous membranes, it produces
pain and breathing difficulty, discouraging protestors and assailants.
Refer to the
Scoville scale for a comparison of pepper spray to other
sources of capsaicin.
Capsaicin is also used to deter pests, specifically mammalian pests.
Targets of capsaicin repellants include voles, deer, rabbits,
squirrels, bears, insects, and attacking dogs. Ground or crushed
dried chili pods may be used in birdseed to deter rodents, taking
advantage of the insensitivity of birds to capsaicin. The Elephant
Pepper Development Trust claims the use of chili peppers to improve
crop security for rural African communities. Notably,
an article published in the Journal of Environmental Science and
Health in 2006 states that "Although hot chili pepper extract is
commonly used as a component of household and garden insect-repellent
formulas, it is not clear that the capsaicinoid elements of the
extract are responsible for its repellency."
The first pesticide product using solely capsaicin as the active
ingredient was registered with the U.S. Department of Agriculture in
Capsaicin is a banned substance in equestrian sports because of its
hypersensitizing and pain-relieving properties. At the show jumping
events of the 2008 Summer Olympics, four horses tested positive for
the substance, which resulted in disqualification.
Mechanism of action
The burning and painful sensations associated with capsaicin result
from its chemical interaction with sensory neurons. Capsaicin, as a
member of the vanilloid family, binds to a receptor called the
vanilloid receptor subtype 1 (TRPV1). First cloned in 1997, TRPV1
is an ion channel-type receptor. TRPV1, which can also be
stimulated with heat, protons and physical abrasion, permits cations
to pass through the cell membrane when activated. The resulting
depolarization of the neuron stimulates it to signal the brain. By
binding to the
TRPV1 receptor, the capsaicin molecule produces similar
sensations to those of excessive heat or abrasive damage, explaining
why the spiciness of capsaicin is described as a burning sensation.
Early research showed capsaicin to evoke a long-onset current in
comparison to other chemical agonists, suggesting the involvement of a
significant rate-limiting factor. Subsequent to this, the TRPV1
ion channel has been shown to be a member of the superfamily of TRP
ion channels, and as such is now referred to as TRPV1. There are a
number of different TRP ion channels that have been shown to be
sensitive to different ranges of temperature and probably are
responsible for our range of temperature sensation. Thus, capsaicin
does not actually cause a chemical burn, or indeed any direct tissue
damage at all, when chili peppers are the source of exposure. The
inflammation resulting from exposure to capsaicin is believed to be
the result of the body's reaction to nerve excitement. For example,
the mode of action of capsaicin in inducing bronchoconstriction is
thought to involve stimulation of C fibers culminating in the
release of neuropeptides. In essence, the body inflames tissues as if
it has undergone a burn or abrasion and the resulting inflammation can
cause tissue damage in cases of extreme exposure, as is the case for
many substances that cause the body to trigger an inflammatory
Acute health effects
Capsaicin is a strong irritant requiring proper protective goggles,
respirators, and proper hazardous material-handling procedures.
Capsaicin takes effect upon skin contact (irritant, sensitizer), eye
contact (irritant), ingestion, and inhalation (lung irritant, lung
sensitizer). LD50 in mice is 47.2 mg/kg.
Painful exposures to capsaicin-containing peppers are among the most
common plant-related exposures presented to poison centers. They
cause burning or stinging pain to the skin and, if ingested in large
amounts by adults or small amounts by children, can produce nausea,
vomiting, abdominal pain, and burning diarrhea. Eye exposure produces
intense tearing, pain, conjunctivitis, and blepharospasm.
When used for weight loss in capsules, there has been a report of
heart attack; this was thought to be due to excess sympathetic
Treatment after exposure
The primary treatment is removal from exposure. Contaminated clothing
should be removed and placed in airtight bags to prevent secondary
For external exposure, bathing the mucous membrane surfaces that have
contacted capsaicin with oily compounds such as vegetable oil,
paraffin oil, petroleum jelly (Vaseline), creams, or polyethylene
glycol is the most effective way to attenuate the associated
discomfort; since oil and capsaicin are both
hydrophobic hydrocarbons the capsaicin that has not already been
absorbed into tissues will be picked up into solution and easily
Capsaicin can also be washed off the skin using soap,
shampoo, or other detergents. Plain water is ineffective at removing
capsaicin, as are bleach, sodium metabisulfite and topical antacid
Capsaicin is soluble in alcohol, which
can be used to clean contaminated items.
When capsaicin is ingested, cold milk is an effective way to relieve
the burning sensation (due to caseins having a detergent effect on
capsaicin); and room-temperature sugar solution (10%) at
20 °C (68 °F) is almost as effective. The burning
sensation will slowly fade away over several hours if no actions are
Capsaicin-induced asthma might be treated with oral antihistamines or
Effects on weight loss and regain
There is no evidence showing that weight loss is directly correlated
with ingesting capsaicin. Well-designed clinical studies have not been
performed because the pungency of capsaicin in prescribed doses under
research prevents subject compliance.
Allicin, the active piquant flavor chemical in uncooked garlic, and to
a lesser extent onions (see those articles for discussion of other
chemicals in them relating to pungency, and eye irritation)
Allyl isothiocyanate (also allyl mercaptan), the active piquant
chemical in mustard, radishes, horseradish, and wasabi
Capsazepine, capsaicin antagonist
Gingerol and shogaol, the active piquant flavor chemicals in ginger
List of investigational analgesics
Naga Viper pepper, Bhut Jolokia Pepper, Carolina Reaper, Trinidad
Moruga Scorpion; some of the world's most capsaicin-rich fruits
Resiniferatoxin, an ultrapotent capsaicin analog in
syn-Propanethial-S-oxide, the major active piquant chemical in onions
Piperine, the active piquant flavor chemical in black pepper
ChemSpider – Capsaicin
^ a b 
^ What Made Chili Peppers So Spicy?
Talk of the Nation, 15 August
^ History of early research on capsaicin:
Harvey W. Felter and John U. Lloyd, King's American Dispensatory
(Cincinnati, Ohio: Ohio Valley Co., 1898), vol. 1, page 435. Available
on-line at: Henriette's Herbal.
Andrew G. Du Mez, "A century of the United States pharmocopoeia
1820–1920. I. The galenical oleoresins" (Ph.D. dissertation,
University of Wisconsin, 1917), pages 111–132. Available on-line at:
C. F. Bucholz (1816) "Chemische Untersuchung der trockenen reifen
spanischen Pfeffers" [Chemical investigation of dry, ripe Spanish
peppers], Almanach oder Taschenbuch für Scheidekünstler und
Apotheker (Weimar) [Almanac or Pocket-book for Analysts (Chemists) and
Apothecaries], vol. 37, pages 1–30. [Note: Christian Friedrich
Bucholz's surname has been variously spelled as "Bucholz", "Bucholtz",
The results of Bucholz's and Braconnot's analyses of
appear in: Jonathan Pereira, The Elements of Materia Medica and
Therapeutics, 3rd U.S. ed. (Philadelphia, Pennsylvania: Blanchard and
Lea, 1854), vol. 2, page 506.
Biographical information about Christian Friedrich Bucholz is
available in: Hugh J. Rose, Henry J. Rose, and Thomas Wright, ed.s, A
New General Biographical Dictionary (London, England: 1857), vol. 5,
Biographical information about C. F. Bucholz is also available (in
German) on-line at: Allgemeine Deutsche Biographie.
Some other early investigators who also extracted the active component
Benjamin Maurach (1816) "Pharmaceutisch-chemische Untersuchung des
spanischen Pfeffers" (Pharmaceutical-chemical investigation of Spanish
peppers), Berlinisches Jahrbuch für die Pharmacie, vol. 17, pages
63–73. Abstracts of Maurach's paper appear in: (i) Repertorium für
die Pharmacie, vol. 6, page 117-119 (1819); (ii) Allgemeine
Literatur-Zeitung, vol. 4, no. 18, page 146 (Feb. 1821); (iii)
"Spanischer oder indischer Pfeffer", System der Materia medica ...,
vol. 6, pages 381–386 (1821) (this reference also contains an
abstract of Bucholz's analysis of peppers).
Henri Braconnot (1817) "Examen chemique du Piment, de
son principe âcre, et de celui des plantes de la famille des
renonculacées" (Chemical investigation of the chili pepper, of its
pungent principle [constituent, component], and of that of plants of
the family Ranunculus), Annales de Chemie et de Physique, vol. 6,
pages 122- 131.
Johann Georg Forchhammer
Johann Georg Forchhammer in: Hans C. Oersted (1820)
"Sur la découverte de deux nouveaux alcalis végétaux" (On the
discovery of two new plant alkalis), Journal de physique, de chemie,
d'histoire naturelle et des arts, vol. 90, pages 173–174.
German apothecary Ernst Witting (1822) "Considerations sur les bases
vegetales en general, sous le point de vue pharmaceutique et
descriptif de deux substances, la capsicine et la nicotianine"
(Thoughts on the plant bases in general from a pharmaceutical
viewpoint, and description of two substances, capsicin and nicotine),
Beiträge für die pharmaceutische und analytische Chemie, vol. 3,
^ In a series of articles, J. C. Thresh obtained capsaicin in almost
J. C. Thresh (1876) "Isolation of capsaicin," The Pharmaceutical
Journal and Transactions, 3rd series, vol. 6, pages 941–947;
J. C. Thresh (8 July 1876) "Capsaicin, the active principle in
Capsicum fruits," The Pharmaceutical Journal and Transactions, 3rd
series, vol. 7, no. 315, pages 21 ff. [Note: This article is
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Abdel-Salam, Omar M. E. [ed.]:
Capsaicin as a
Springer, 2014. ISBN 978-3-0348-0827-9 (print);
ISBN 978-3-0348-0828-6 (eBook).
Wikimedia Commons has media related to Capsaicin.
Look up capsaicin in Wiktionary, the free dictionary.
Capsaicin Technical Fact Sheet – National Pesticide Information
Fire and Spice: The molecular basis for flavor
TRP channel modulators
Sanshool (ginger, Sichuan and melegueta peppers)
Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
CR gas (dibenzoxazepine; DBO)
CS gas (2-chlorobenzal malononitrile)
Farnesyl thiosalicylic acid
Ligustilide (celery, Angelica acutiloba)
Linalool (Sichuan pepper, thyme)
Methyl salicylate (wintergreen)
Oleocanthal (olive oil)
Paclitaxel (Pacific yew)
Polygodial (Dorrigo pepper)
Shogaols (ginger, Sichuan and melegueta peppers)
Thiopropanal S-oxide (onion)
Umbellulone (Umbellularia californica)
Adhyperforin (St John's wort)
Hyperforin (St John's wort)
Cooling Agent 10
Rutamarin (Ruta graveolens)
Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
Rutamarin (Ruta graveolens)
Triptolide (Tripterygium wilfordii)
Sanshool (ginger, Sichuan and melegueta peppers)
Bisandrographolide (Andrographis paniculata)
Camphor (camphor laurel, rosemary, camphorweed, African blue basil,
Capsaicin (chili pepper)
Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
Dihydrocapsaicin (chili pepper)
Eugenol (basil, clove)
Evodiamine (Euodia ruticarpa)
Homocapsaicin (chili pepper)
Homodihydrocapsaicin (chili pepper)
Low pH (acidic conditions)
Nonivamide (PAVA) (PAVA spray)
Nordihydrocapsaicin (chili pepper)
Paclitaxel (Pacific yew)
Phorbol esters (e.g., 4α-PDD)
Piperine (black pepper, long pepper)
Polygodial (Dorrigo pepper)
Rutamarin (Ruta graveolens)
Resiniferatoxin (RTX) (
Shogaols (ginger, Sichuan and melegueta peppers)
Thymol (thyme, oregano)
Cannabigerolic acid (cannabis)
See also: Receptor/signaling modulators •
Ion channel modulators